A denim jacket can look cheap, and it can look a little juvenile, but Rihanna managed to find a version with some edge (okay, those are inch-long spikes!) and wear it with class. No surprise there.
Pairing a perennially trendy item like a denim jacket with something classic like a simple black dress or jeans and a simple top is always the way to go. And remember crew necklines look best with those collars, where a deep-V may accentuate the trailer park possibilities of the look.